反応 #312598

反応方程式

water

5-benzylthio-3-chloro-1-methylpyrazole-4-carboxylic acid chloride

allyloxyamine hydrochloride

triethylamine

→

desired product

収率 101.5%

(5-benzylthio-3-chloro-1-methylpyrazol-4-yl)-N-allyloxycarboxylic acid amide

収率 101.5%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added at 0° C.
2. 2
   workup.STIRRINGAfter stirring at room temperature for 1 hour
3. 3
   抽出extracted with ethyl acetate
4. 4
   洗浄The resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off

実験手順

In a suspension of allyloxyamine hydrochloride (2.3 g, 21 mmol) in tetrahydrofuran (20 ml), 2.9 g (29 mmol) of triethylamine was added at 0° C., stirred at room temperature for 5 minutes and then a solution of 5-benzylthio-3-chloro-1-methylpyrazole-4-carboxylic acid chloride (2.1 g, 7.0 mmol) in tetrahydrofuran (10 ml) was added dropwise. After stirring at room temperature for 1 hour, water (100 ml) was added and extracted with ethyl acetate. The resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and the solvent was distilled off to obtain the desired product (2.4 g). Oily substance. Proton nuclear magnetic resonance chemical shift values δ (ppm) (in CDCl3) 3.45 (s, 3H), 4.11 (s, 2H), 4.53 (d, J=6.3 Hz, 2H), 5.34-5.45 (m, 2H), 6.00-6.13 (m, 1H), 7.03-7.06 (m, 2H), 7.24-7.28 (m, 3H), 9.14 (brs, 1H).

出典